Title: Winsor Vacation Home Rentals from CA $92: Search Top Private Vacation Homes for Rent | Expedia.ca [Winsor Travel Guide](https://expedia.ca/Winsor.dx3000381484)[Hotels in Winsor](https://expedia.ca/Winsor-Hotels.d3000381484.Travel-Guide-Hotels)[Vacation Rentals in Winsor](https://expedia.ca/Winsor-Vacation-Rentals.d3000381484.Travel-Guide-VacationRentals)[Winsor Car Rentals](https://expedia.ca/Car-Rentals-In-Winsor.d3000381484.Car-Rental-Guide)[Winsor Vacation Packages](https://expedia.ca/Winsor.d3000381484.Destination-Travel-Guides) ![Default HTG hotel image](https://media.expedia.com/media/content/shared/images/travelguides/sem-hotels-tablet.jpg?impolicy=fcrop&w=1200&h=500&q=medium) # Winsor Vacation Rentals ![](https://a.travel-assets.com/travel-assets-manager/pictogram-bex/light__calendar_shield.svg) ### Change your mind Book hotels with free cancellation ![](https://a.travel-assets.com/travel-assets-manager/pictogram-bex/light__deals.svg) ### Treat yourself Sign in to save 10% or more on thousands of hotels [Sign in](https://www.expedia.ca/login) ![](https://a.travel-assets.com/travel-assets-manager/pictogram-bex/light__bed.svg) ### Be picky Search almost a million properties worldwide ## Check prices for these dates Next weekend [Oct 24 - Oct 26](https://www.expedia.ca/Hotel-Search?regionId=3000381484&startDate=2025-10-24&endDate=2025-10-26&adults=2&categorySearch=vacation_rentals_option&stay_options_group=vacation_rentals_option&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) In two weeks [Oct 31 - Nov 2](https://www.expedia.ca/Hotel-Search?regionId=3000381484&startDate=2025-10-31&endDate=2025-11-02&adults=2&categorySearch=vacation_rentals_option&stay_options_group=vacation_rentals_option&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) In one month [Nov 14 - Nov 16](https://www.expedia.ca/Hotel-Search?regionId=3000381484&startDate=2025-11-14&endDate=2025-11-16&adults=2&categorySearch=vacation_rentals_option&stay_options_group=vacation_rentals_option&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) In two months [Dec 12 - Dec 14](https://www.expedia.ca/Hotel-Search?regionId=3000381484&startDate=2025-12-12&endDate=2025-12-14&adults=2&categorySearch=vacation_rentals_option&stay_options_group=vacation_rentals_option&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) ## Browse Select Winsor Vacation Homes ![Exterior](https://images.trvl-media.com/lodging/7000000/6180000/6175200/6175183/ce714431.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Executive Double Room, Ensuite, Sea View (Plymouth)](https://images.trvl-media.com/lodging/7000000/6180000/6175200/6175183/fd724375.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Bar (on property)](https://images.trvl-media.com/lodging/7000000/6180000/6175200/6175183/9391f155.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Bar (on property)](https://images.trvl-media.com/lodging/7000000/6180000/6175200/6175183/ec85f2da.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### The Cliff House Hotel New Milton 9.4/10 Exceptional (398) "Great location, food, accomodation and pleasant staff." CA $265 CA $318 total includes taxes & fees Oct 16 - Oct 17 [](https://www.expedia.ca/New-Milton-Hotels-The-Cliff-House-Hotel.h6175183.Hotel-Information) ![Smart TV](https://images.trvl-media.com/lodging/114000000/113940000/113932900/113932890/84ac05ef.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Interior](https://images.trvl-media.com/lodging/114000000/113940000/113932900/113932890/22c63f56.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![2 bedrooms, desk, iron/ironing board, free WiFi](https://images.trvl-media.com/lodging/114000000/113940000/113932900/113932890/70c13f4b.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/114000000/113940000/113932900/113932890/214190d7.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### The Enchanting Silver Birch Retreat, New Forest Southampton 10/10 Exceptional (1) "Exceptional new renovation. Spectacular kitchen facilities and provisions. Great location for access to The New Forest. Wish we were staying here longer. One of the best properties of our trip. " CA $166 CA $338 total includes taxes & fees Oct 19 - Oct 20 [](https://www.expedia.ca/Southampton-Hotels-The-Enchanting-Silver-Birch-Retreat.h113932890.Hotel-Information) ![Interior](https://images.trvl-media.com/lodging/114000000/113940000/113932500/113932435/e5ace06e.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Miscellaneous](https://images.trvl-media.com/lodging/114000000/113940000/113932500/113932435/8e4e4bfd.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![2 bedrooms, iron/ironing board, free WiFi, bed sheets](https://images.trvl-media.com/lodging/114000000/113940000/113932500/113932435/db9e43db.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Smart TV](https://images.trvl-media.com/lodging/114000000/113940000/113932500/113932435/990035d9.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### The Charming Redwood Escape, New Forest Southampton 10/10 Exceptional (1) "Lovely place to stay. Right next to the new forest national park with easy access to so many nearby attractions. Will definitely return again. " CA $243 CA $432 total includes taxes & fees Oct 29 - Oct 30 [](https://www.expedia.ca/Southampton-Hotels-Charming-Redwood-Escape.h113932435.Hotel-Information) ![Fridge, microwave, oven, dishwasher](https://images.trvl-media.com/lodging/110000000/109110000/109109100/109109004/43ccc555.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/110000000/109110000/109109100/109109004/c6f57347.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Smart TV](https://images.trvl-media.com/lodging/110000000/109110000/109109100/109109004/2acfa574.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![2 bedrooms, iron/ironing board, WiFi, bed sheets](https://images.trvl-media.com/lodging/110000000/109110000/109109100/109109004/24e109ac.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Beautiful 2 bedroom full-furnished semi-detached house with parking Dibden Purlieu 9.4/10 Exceptional (6) "Great location, xxx" CA $211 CA $240 total includes taxes & fees Oct 15 - Oct 16 [](https://www.expedia.ca/Southampton-Hotels-Beautiful-2-Bedroom-Full-Furnished-Semi-Detached-House-With-Parking.h109109004.Hotel-Information) ![Property amenity](https://images.trvl-media.com/lodging/34000000/33380000/33377500/33377494/3cab1d66.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Deluxe Apartment, Multiple Beds, Non Smoking | Interior](https://images.trvl-media.com/lodging/34000000/33380000/33377500/33377494/cb07ec4b.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Deluxe Apartment, Multiple Beds, Non Smoking | In-room dining](https://images.trvl-media.com/lodging/34000000/33380000/33377500/33377494/6fc05d61.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Point of interest](https://images.trvl-media.com/lodging/34000000/33380000/33377500/33377494/08670b39.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Holiday Home With Hot Tub & Sauna Bournemouth 9.0/10 Wonderful (4) " What the full holiday with my kids thanks guys" CA $252 CA $639 total includes taxes & fees Oct 20 - Oct 21 [](https://www.expedia.ca/Bournemouth-Hotels-Holiday-Home-With-Hot-Tub-Sauna.h33377494.Hotel-Information) ![Dining](https://images.trvl-media.com/lodging/74000000/73450000/73441000/73440982/273cf557.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Smart TV, books](https://images.trvl-media.com/lodging/74000000/73450000/73441000/73440982/cfc1b571.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![2 bedrooms, desk, iron/ironing board, WiFi](https://images.trvl-media.com/lodging/74000000/73450000/73441000/73440982/337366a6.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior detail](https://images.trvl-media.com/lodging/74000000/73450000/73441000/73440982/7fe23adb.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### The Nautilus -Cowes IOW- 2 bedroom bungalow/garden Cowes Isle of Wight 10/10 Exceptional (4) "Unassuming from the outside, excellently decorated and equipped internally, including a nice garden." CA $187 CA $397 total includes taxes & fees Nov 1 - Nov 2 [](https://www.expedia.ca/Cowes-Hotels-The-Nautilus-Cowes-IOW-2-Bedroom-Bungalowgarden.h73440982.Hotel-Information) ![Smart TV, books, stereo](https://images.trvl-media.com/lodging/114000000/113880000/113877800/113877774/304c4d23.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/114000000/113880000/113877800/113877774/13bd4782.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/114000000/113880000/113877800/113877774/7e779d3b.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Terrace/patio](https://images.trvl-media.com/lodging/114000000/113880000/113877800/113877774/9b1d12da.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Peaceful barn stay near Lymington with private garden Lymington 8.0/10 Very good (1) "Great host and property had a lovely stay" CA $251 CA $382 total includes taxes & fees Nov 11 - Nov 12 [](https://www.expedia.ca/Lymington-Hotels-Beautiful-Escape-In-New-Forest-With-Hot-Hub.h113877774.Hotel-Information) ![Terrace/patio](https://images.trvl-media.com/lodging/25000000/24920000/24910200/24910197/762189db.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![1 bedroom, desk, soundproofing, WiFi](https://images.trvl-media.com/lodging/25000000/24920000/24910200/24910197/4fdd4e45.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Interior](https://images.trvl-media.com/lodging/25000000/24920000/24910200/24910197/53b70ccd.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/25000000/24920000/24910200/24910197/d02626dc.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Luxury shepherd's hut Bransgore 9.8/10 Exceptional (40) "Great little place in great location plenty of space to relax and unwind" CA $225 CA $254 total includes taxes & fees Oct 15 - Oct 16 [](https://www.expedia.ca/Christchurch-Hotels-Luxury-Shepherds-Hut.h24910197.Hotel-Information) ![1 bedroom, WiFi, bed sheets](https://images.trvl-media.com/lodging/107000000/106550000/106544900/106544866/5ca6fe26.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![1 bedroom, WiFi, bed sheets](https://images.trvl-media.com/lodging/107000000/106550000/106544900/106544866/61e09019.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Bathroom](https://images.trvl-media.com/lodging/107000000/106550000/106544900/106544866/03746b2a.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Miscellaneous](https://images.trvl-media.com/lodging/107000000/106550000/106544900/106544866/c1f4e0d5.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Cosy En-suite Room in the City Centre Room 14 Freemantle CA $52 CA $92 total includes taxes & fees Nov 9 - Nov 10 [](https://www.expedia.ca/Southampton-Hotels-Cosy-En-Suite-Room-In-The-City-Centre-Room-14.h106544866.Hotel-Information) ![1 bedroom, WiFi](https://images.trvl-media.com/lodging/122000000/121080000/121072400/121072395/507fe50a.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![1 bedroom, WiFi](https://images.trvl-media.com/lodging/122000000/121080000/121072400/121072395/2051ca86.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![1 bedroom, WiFi](https://images.trvl-media.com/lodging/122000000/121080000/121072400/121072395/4a91eefb.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![1 bedroom, WiFi](https://images.trvl-media.com/lodging/122000000/121080000/121072400/121072395/94c3d647.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Darwin road guest house room 3 Freemantle CA $45 CA $45 total includes taxes & fees Nov 9 - Nov 10 [](https://www.expedia.ca/Southampton-Hotels-Darwin-Road-Guest-House-Room-3.h121072395.Hotel-Information) ![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/75000000/74840000/74837700/74837623/6788a072.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Smart TV](https://images.trvl-media.com/lodging/75000000/74840000/74837700/74837623/32b4d3de.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Outdoor dining](https://images.trvl-media.com/lodging/75000000/74840000/74837700/74837623/ca9d1ada.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/75000000/74840000/74837700/74837623/7064040d.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### 3 Bedrooms house ideal for long Stays! Southampton 10/10 Exceptional (3) "Great location, lovely clean property can recommend." CA $199 CA $313 total includes taxes & fees Oct 19 - Oct 20 [](https://www.expedia.ca/Southampton-Hotels-Perfect-For-Contractors.h74837623.Hotel-Information) ![1 bedroom, desk, free WiFi, bed sheets](https://images.trvl-media.com/lodging/120000000/119440000/119437700/119437634/77857bc8.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/120000000/119440000/119437700/119437634/68492b39.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/120000000/119440000/119437700/119437634/baf83d09.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/120000000/119440000/119437700/119437634/b265778b.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Historic studio annexe for two with New Forest on your doorstep Burgate CA $128 CA $184 total includes taxes & fees Oct 16 - Oct 17 [](https://www.expedia.ca/Fordingbridge-Hotels-Historic-Studio-Annexe-For-Two-With-New-Forest-On-Your-Doorstep.h119437634.Hotel-Information) ![Property grounds](https://images.trvl-media.com/lodging/106000000/105350000/105346900/105346886/934db791.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/106000000/105350000/105346900/105346886/25a84a40.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Property grounds](https://images.trvl-media.com/lodging/106000000/105350000/105346900/105346886/72aa98f2.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![2 bedrooms, iron/ironing board, travel crib, free WiFi](https://images.trvl-media.com/lodging/106000000/105350000/105346900/105346886/c1a0c8a8.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### modern Bungalow with hot tub, garden, bbq & Netflix 10 min drive to city centre Southampton 10/10 Exceptional (3) "The accommodation was very comfortable and perfectly situated for a pre cruise stay! The beds were comfortable and the kitchen was very well equipped! Comfy sofas in the lounge and great internet! Highly recommended! Would definitely book again! Great host too! " CA $303 CA $473 total includes taxes & fees Oct 20 - Oct 21 [](https://www.expedia.ca/Southampton-Hotels-Modern-Bungalow-With-Hot-Tub.h105346886.Hotel-Information) ![Luxury House](https://images.trvl-media.com/lodging/103000000/102630000/102626100/102626005/51c0cd55.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Hot stone massages, deep-tissue massages, Swedish massages](https://images.trvl-media.com/lodging/103000000/102630000/102626100/102626005/8f3ac127.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Luxury House | Living area](https://images.trvl-media.com/lodging/103000000/102630000/102626100/102626005/d488f49c.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Luxury House | Living area](https://images.trvl-media.com/lodging/103000000/102630000/102626100/102626005/b6b3410f.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Pamper House Holiday Home And Annex Ferndown CA $1,142 CA $1,895 total includes taxes & fees Nov 3 - Nov 4 [](https://www.expedia.ca/Ferndown-Hotels-Pamper-House-Holiday-Home-And-Annex.h102626005.Hotel-Information) ![Private kitchen](https://images.trvl-media.com/lodging/105000000/104820000/104814800/104814707/df396534.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Dining](https://images.trvl-media.com/lodging/105000000/104820000/104814800/104814707/0bf0246e.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![4 bedrooms, WiFi](https://images.trvl-media.com/lodging/105000000/104820000/104814800/104814707/1e9d002e.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Outdoor dining](https://images.trvl-media.com/lodging/105000000/104820000/104814800/104814707/03fa8e02.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Homely 4 Bedroom large house inc free parking Bournemouth 7.0/10 Good (2) CA $185 CA $382 total includes taxes & fees Oct 19 - Oct 20 [](https://www.expedia.ca/Bournemouth-Hotels-Homely-4-Bedroom-Large-House-Inc-Free-Parking.h104814707.Hotel-Information) ![Exterior detail](https://images.trvl-media.com/lodging/120000000/119950000/119949600/119949570/w4000h2660x0y0-345e4fa3.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Interior](https://images.trvl-media.com/lodging/120000000/119950000/119949600/119949570/w4000h2785x0y0-61dd061a.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Smart TV, books](https://images.trvl-media.com/lodging/120000000/119950000/119949600/119949570/w4000h2788x0y0-c737abd7.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Interior](https://images.trvl-media.com/lodging/120000000/119950000/119949600/119949570/w4000h2784x0y0-f2a3612e.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Porcupine Cave : Ensuite /self\_check in /private entrance / private parking. Fareham CA $135 CA $165 total includes taxes & fees Nov 12 - Nov 13 [](https://www.expedia.ca/Fareham-Hotels-Porcupine-Cave-Ensuite-Selfcheck-In-Private-Entrance-Private-Parking.h119949570.Hotel-Information) ![Microwave, oven, stovetop, dishwasher](https://images.trvl-media.com/lodging/109000000/108020000/108015200/108015134/bc498b35.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Interior](https://images.trvl-media.com/lodging/109000000/108020000/108015200/108015134/a1891167.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![1 bedroom, desk, iron/ironing board, WiFi](https://images.trvl-media.com/lodging/109000000/108020000/108015200/108015134/10c4396c.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/109000000/108020000/108015200/108015134/26a5cbd1.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Wilmer House Eastleigh 6.0/10 (1) "Paid £74 for a room with no kettle or TV, and wasn't even ensuit, so for me the price was about £24 too much, the bathroom was right next to my room, and the girl in another room was in and out to the bathroom all night, and then decided she was going to have a shower at 6.30am and then dry her hair, the room was comfortable and there was a kitchen and TV downstairs but nowhere to sit and watch TV as. The 1 armchair was covered in laundry and I didn't fancy sitting on a stool at the kitchen... CA $94 CA $124 total includes taxes & fees Oct 17 - Oct 18 [](https://www.expedia.ca/Eastleigh-Hotels-Wilmer-Guest-House.h108015134.Hotel-Information) ![Beach](https://images.trvl-media.com/lodging/47000000/46380000/46377900/46377871/e287f160.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Outdoor spa tub](https://images.trvl-media.com/lodging/47000000/46380000/46377900/46377871/90ad4f35.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![3 bedrooms, iron/ironing board, travel crib, WiFi](https://images.trvl-media.com/lodging/47000000/46380000/46377900/46377871/b58b4f5b.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![TV, DVD player](https://images.trvl-media.com/lodging/47000000/46380000/46377900/46377871/e2d6a6d9.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Holiday home hot tub and sauna Bournemouth 8.8/10 Excellent (5) "We had a brilliant time over Christmas 2023. The home was very clean and comfortable with everything we needed. Would love to stay again. Great location too." CA $309 CA $646 total includes taxes & fees Oct 20 - Oct 21 [](https://www.expedia.ca/Bournemouth-Hotels-Holiday-Home-With-Hot-Tub-Sauna.h46377871.Hotel-Information) ![Bungalow, 2 Bedrooms, Patio, City View | Property grounds](https://images.trvl-media.com/lodging/117000000/116890000/116880800/116880757/77a230a9.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Bungalow, 2 Bedrooms, Patio, City View](https://images.trvl-media.com/lodging/117000000/116890000/116880800/116880757/30230e2a.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Bungalow, 2 Bedrooms, Patio, City View | Laundry](https://images.trvl-media.com/lodging/117000000/116890000/116880800/116880757/14bdbf9a.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Bungalow, 2 Bedrooms, Patio, City View | Interior](https://images.trvl-media.com/lodging/117000000/116890000/116880800/116880757/10d660bb.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Peaceful Retreat in Southampton's Countryside Southampton CA $307 CA $454 total includes taxes & fees Oct 21 - Oct 22 [](https://www.expedia.ca/Southampton-Hotels-Peaceful-Retreat-In-Southamptons-Countryside.h116880757.Hotel-Information) ![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/96000000/95210000/95201900/95201827/5e1a4dd1.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Dining](https://images.trvl-media.com/lodging/96000000/95210000/95201900/95201827/647dbab6.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Beach](https://images.trvl-media.com/lodging/96000000/95210000/95201900/95201827/9335c9bc.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Terrace/patio](https://images.trvl-media.com/lodging/96000000/95210000/95201900/95201827/6ea2f3d3.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### 4-bedroom house in prime location Hampshire 10/10 Exceptional (2) "Had a lovely weekend. Lovely quiet place to stay. X" CA $466 CA $716 total includes taxes & fees Oct 16 - Oct 17 [](https://www.expedia.ca/Southampton-Hotels-4-Bedroom-House-In-Prime-Location.h95201827.Hotel-Information) Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply. [View all properties](https://expedia.ca/Hotel-Search?startDate=2025-10-28&endDate=2025-10-29®ionId=3000381484&adults=2&categorySearch=vacation_rentals_option&stay_options_group=vacation_rentals_option&openPlayBack=true) ![](https://a.travel-assets.com/pricing-claim/sparkle_dark.svg) Save an average of 15% on thousands of hotels when you're signed in [Sign in](https://expedia.ca/user/signin?ckoflag=0&uurl=e3id%3Dredr%26rurl%3D%2FWinsor-Private-Vacation-Homes.d3000381484-aaPrivateVacationHomes.Travel-Guide-Accommodation)[Sign up, it's free](https://expedia.ca/signup?enable_registration=true&+=&uurl=e3id%3Dredr%26rurl%3D%2FWinsor-Private-Vacation-Homes.d3000381484-aaPrivateVacationHomes.Travel-Guide-Accommodation) ## Top Winsor Hotel Reviews ![The Winchester Hotel & Spa](//images.trvl-media.com/lodging/1000000/30000/26100/26080/4127003a_y.jpg) ### The Winchester Hotel & Spa 10/10 Excellent "." [](https://expedia.ca/Winchester-Hotels-The-Winchester-Hotel-Spa.h26080.Hotel-Information) ![Harbour Hotel Southampton](//images.trvl-media.com/lodging/20000000/19510000/19504400/19504324/68c45722_y.jpg) ### Harbour Hotel Southampton 10/10 Excellent "Not so good due to staffing in some ateas" [](https://expedia.ca/Southampton-Hotels-Southampton-Harbour-Hotel.h19504324.Hotel-Information) ![room2 Southampton Hometel](//images.trvl-media.com/lodging/23000000/22610000/22608700/22608660/884f1de7_y.jpg) ### room2 Southampton Hometel 10/10 Excellent "Friendly staff, good breakfast, easy parking, comfortable bed" [](https://expedia.ca/Southampton-Hotels-Room2-Southampton.h22608660.Hotel-Information) ![Winchester Wessex Hotel by Sunday](//images.trvl-media.com/lodging/1000000/10000/4800/4799/3ac6caac_y.jpg) ### Winchester Wessex Hotel by Sunday 10/10 Excellent "No car parking spaces " [](https://expedia.ca/Winchester-Hotels-Winchester-Wessex-Hotel-By-Sunday.h4799.Hotel-Information) ![Leonardo Hotel Southampton ](//images.trvl-media.com/lodging/2000000/1180000/1178300/1178290/0c96afed_y.jpg) ### Leonardo Hotel Southampton 10/10 Excellent "Stayed here night before my cruise and was very nice " [](https://expedia.ca/Southampton-Hotels-Jurys-Inn-Southampton.h1178290.Hotel-Information) ![Leonardo Royal Southampton Grand Harbour](//images.trvl-media.com/lodging/1000000/20000/20000/19955/662fccb6_y.jpg) ### Leonardo Royal Southampton Grand Harbour 10/10 Excellent "We were thrilled to have room 119 which had a balcony and we could view the cruise ships departing. It was warm and clean. The complimentary water and coffee pods were really appreciated. Service at breakfast and at reception was warm, friendly and efficient. It was a surprise that breakfast and parking were included. Had a lovely reunion evening with tasty food, especially the beef. Well done all " [](https://expedia.ca/Southampton-Hotels-Leonardo-Royal-Southampton-Grand-Harbour.h19955.Hotel-Information) ![Moxy Southampton](//images.trvl-media.com/lodging/43000000/42110000/42101700/42101688/92beb57c_y.jpg) ### Moxy Southampton 10/10 Excellent "Chambre petite mais propre et confortable. Personnel accueillant." [](https://expedia.ca/Southampton-Hotels-Moxy-By-Marriott-Southampton.h42101688.Hotel-Information) ![Holiday Inn Express Southampton M27 Jct7 by IHG](//images.trvl-media.com/lodging/1000000/980000/977300/977282/fc514007_y.jpg) ### Holiday Inn Express Southampton M27 Jct7 by IHG 10/10 Excellent "From checking in to checkout the service was excellent. In particular Gemma on reception was very helpful. Very busy hotel with a lot of children staying. As long as you don’t mind noise in the restaurant area it’s an ideal hotel for staying over for one night. " [](https://expedia.ca/Southampton-Hotels-Holiday-Inn-Express-Southampton-M27-Jct7.h977282.Hotel-Information) ![voco Southampton by IHG](//images.trvl-media.com/lodging/1000000/20000/17500/17411/821a0cfd_y.jpg) ### voco Southampton by IHG 10/10 Excellent "Great place staff friendly " [](https://expedia.ca/Southampton-Hotels-Voco-Southampton-By-IHG.h17411.Hotel-Information) ## Find out more about Winsor ## Winsor Vacation Homes information | Number of reviews | 464 | | --- | --- | | Accommodation | 488 Vacation Homes | | Lowest Price | CA $92 | | Highest Price | CA $1,895 |